Bumping an old thread. My chukka boot wearing period has all but come to an end. I have sold all my desert and chukkas. For years I wore them and I almost always felt self conscience wearing them. I always feel hobbit like and I don't know, I just overall felt unoriginal. In any event, I am working back down to the ultimate 5 shoe wardrobe. I have two pairs or Santoni Goodyear top shelf lace ups. Brown sleek cap and black brogue punch cap and I treat them like the children I don't have. I have my 5 year old brown Prada Chelsea boots and random other designer low top sneakers.
Every time I wear my Prada Chelsea boots I receive a compliment and even if I don't receive a verbal compliment, women are always checking them out. You know your shoes are good when an older Upper East Side French lady compliments them. Point is why does this happen? Why did I always wear chukkas and women (including my girlfriend) seemed to hate them? I guess the question I'm really asking is has anyone else noticed an adverse reaction from the opposite sex when wearing either boot? I'm 38, but look very youthful and athletic and 5'9 so I've long wondered if chukkas weren't the right boot for my frame.
I'm very close to pulling the trigger on these and considering I've had tremendous success with my current Chelsea's along with their incredible comfort and ease of use, I can't see how I could go wrong. $500 is a lot, for a casual shoe, however.